N-(tert-Butoxycarbonyl)-2-bromoaniline

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-2-bromoaniline
• CAS No.: 78839-75-5
• Molecular Formula: C11H14 Br N O2
• Molecular Weight: 272.142
• Hs Code.: 2924299090
• European Community (EC) Number: 624-859-1
• DSSTox Substance ID: DTXSID10393753
• Nikkaji Number: J782.394K
• Wikidata: Q72510080
• Mol file: 78839-75-5.mol

Synonyms:78839-75-5;N-(tert-Butoxycarbonyl)-2-bromoaniline;tert-Butyl (2-bromophenyl)carbamate;n-boc-2-bromoaniline;tert-butyl N-(2-bromophenyl)carbamate;tert-butyl 2-bromophenylcarbamate;MFCD01006614;SCHEMBL632629;(2-Bromophenyl)carbamic acid, 1,1-dimethylethyl ester;DTXSID10393753;AB8586;AKOS013602727;AM87207;GS-6163;2-Bromo-N-(tert-butoxycarbonyl) aniline;SY041342;2-bromo-N-(tert-Butoxy carbonyl) aniline;N-(tert-Butoxycarbonyl)-2-bromoaniline, 97%;EN300-137912

Chemical Property of N-(tert-Butoxycarbonyl)-2-bromoaniline

Chemical Property:

• Vapor Pressure: 0.00408mmHg at 25°C
• Refractive Index: n20/D 1.54(lit.)
• Boiling Point: 110 °C0.3 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 38.33000
• Density: 1.342 g/mL at 25 °C(lit.)
• LogP: 3.86910
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 271.02079
• Heavy Atom Count: 15
• Complexity: 225

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Boc2-Bromoaniline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=CC=CC=C1Br
• Uses: N-(tert-Butoxycarbonyl)-2-bromoaniline may be used in the synthesis of N-boc-protected o-aryl anilines, which undergoes coupling reaction with bromoacetylenes to form the corresponding arene?ynamides.

Technology Process of N-(tert-Butoxycarbonyl)-2-bromoaniline

There total 11 articles about N-(tert-Butoxycarbonyl)-2-bromoaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-bromoaniline (615-36-1) → 2-bromo-N-(tert-butoxycarbonyl)aniline (78839-75-5)

Guidance literature:

2-bromoaniline; With sodium hydride; In tetrahydrofuran; for 1h; Inert atmosphere; Reflux;

di-tert-butyl dicarbonate; In tetrahydrofuran; for 0.5h; Inert atmosphere;

With sodium hydride; In tetrahydrofuran; Inert atmosphere; Reflux;

DOI:10.1021/ol9020755

Reference yield: 89.0%

tert-butyl ((2-bromobenzoyl)oxy)carbamate → 2-bromo-N-(tert-butoxycarbonyl)aniline (78839-75-5)

Guidance literature:

With caesium carbonate; In acetonitrile; at 20 ℃; for 8h; Sealed tube;

DOI:10.1021/acs.joc.8b00970

Reference yield: 78.0%

tert-butyl phenylcarbamate (3422-01-3) → 2-bromo-N-(tert-butoxycarbonyl)aniline (78839-75-5)

Guidance literature:

tert-butyl phenylcarbamate; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -50 ℃; for 3h;

With carbon tetrabromide; In tetrahydrofuran; pentane; at -75 ℃; Further stages.;

DOI:10.1016/j.jfluchem.2007.09.003

upstream raw materials:

di-tert-butyl dicarbonate

2-bromoaniline

2-bromo-benzoyl azide

tert-butyl alcohol

Downstream raw materials:

N-allyl-N-(t-butoxycarbonyl)-2-bromoaniline

cis-(2-styryl-phenyl)carbamic acid tert-butyl ester

4-(2-aminophenyl)-1-methylpiperidin-4-ol

Refernces

• 1、 Ortuzar, Natalia,Karu, Kersti,Presa, Daniela,Morais, Goreti R.,Sheldrake, Helen M.,Shnyder, Steve D.,Barnieh, Francis M.,Loadman, Paul M.,Patterson, Laurence H.,Pors, Klaus,Searcey, Mark. "Probing cytochrome P450 (CYP) bioactivation with chloromethylindoline bioprecursors derived from the duocarmycin family of compounds". supporting information. . Retrieved 2021/05/04.
• 2、 Flynn, Autumn R.,Mcdaniel, Kelly A.,Hughes, Meredith E.,Vogt, David B.,Jui, Nathan T.. "Hydroarylation of Arenes via Reductive Radical-Polar Crossover". supporting information. p. 9163 - 9168. Retrieved 2020/07/10.